(2R,3R,4R,5R)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-(ethynyl)tetrahydrofuran-3,4-diyl dimethanesulfonate | 1274677-29-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: (2R,3R,4R,5R)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-(ethynyl)tetrahydrofuran-3,4-diyl dimethanesulfonate
• CAS: 1274677-29-0
• 化学式: C₁₂H₁₄N₂O₉S₂
• 分子量: 394.383
• InChiKey: RZVUBNMFXRPGOI-QCNRFFRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.24
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  150.83
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-(ethynyl)tetrahydrofuran-3,4-diyl dimethanesulfonate 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 18.0h， 以86.6%的产率得到1-(5-ethynylfuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of 3′-azido-4′-ethynyl-3′,5′-dideoxy-5′-norarabinouridine: a new anti-HIV nucleoside analogue

  摘要：

  3'-Azido-4'-ethynyl-3',5'dideoxy-5'-norarabinouridine 10 was synthesized from commercial uridine 1 in which the key step is the opening of protected 2',3'-epoxyuridine derivative 7 by sodium azide and the hydroxymethyl at 4-position of the ribose ring are replaced by ethynyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.054
• 作为产物：
  描述：

  (3aS,4S,6R,6aR)-6-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde 在 吡啶 、 正丁基锂 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 29.5h， 生成 (2R,3R,4R,5R)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-(ethynyl)tetrahydrofuran-3,4-diyl dimethanesulfonate
  参考文献：
  名称：

  Synthesis of 3′-azido-4′-ethynyl-3′,5′-dideoxy-5′-norarabinouridine: a new anti-HIV nucleoside analogue

  摘要：

  3'-Azido-4'-ethynyl-3',5'dideoxy-5'-norarabinouridine 10 was synthesized from commercial uridine 1 in which the key step is the opening of protected 2',3'-epoxyuridine derivative 7 by sodium azide and the hydroxymethyl at 4-position of the ribose ring are replaced by ethynyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.054